ChemInform Abstract: Vibrational Spectra, Molecular Structure and Conformations of Organic Azides. Part 5. 3‐Azidopropyne (Propargylazide)

Almloef, Jan; Braathen, Geir; Klæboe, P.; Nielsen, Claus J.; Priebe, H.; Schei, S.H.

doi:10.1002/chin.198746049

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“…Montagnat et al [ 45 ] also synthesized and isolated structurally diverse propargyl azides from aldehydes and alkynes, which also support existence of this key intermediate in Banert cascade reaction ( scheme 3 ). Banert et al also isolated various propargyl azides by previously reported methods [ 7 , 46 ]. Gas phase calculated activation energy barrier (Δ G ‡ ) of TS-A1 is 3.94 kcal mol −1 and the rate of reaction is 8.0 × 10 9 s −1 .…”

Section: Resultsmentioning

confidence: 99%

Theoretical investigation of Banert cascade reaction

Bhattacharyya

Hatua

2018

R. Soc. open sci.

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Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2′-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2′ displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having highest activation energy parameter. Solvent effect on total course of reaction has been found negligible. Furthermore, effects of different density functional theory functionals and functional groups on activation energies of [3,3]-sigmatropic rearrangement of propargyl azide were also studied. BHHLYP, ωB97XD, M062X and BMK calculated ΔG‡ are consistent with B3LYP.

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Section: Resultsmentioning

confidence: 99%